Well put, Nowhere Matt!
Myself, I've been recapitulating phylogeny - seeing all the steps involved in making photography more reliable, automated, less of a chore. Or an appliance, some may say.
I've partially recapitulated the same in audio, building single ended tube amps etc.
One phenomenon that seems to happen is the limitations of the older medium - when it was the only choice - chafed. Now these are a choice. The qualities we've grown up with are familiar and carry a nostalgic fondness. Not to mention, analog signals don't have the hard cut-offs that digital ones do, and thus theoretically one can resolve further into noise.
But this explains why grain and other film artifacts are prized nowadays. And why pop songs will put in exaggerated pops and clicks to evoke a really bad record on a really bad record player
It's also true that we haven't fully acclimated to the limitations and distortions of digital - we're still fairly early in that cycle.
Myself, I'll play LPs but find CDs and nowadays internet radio far more convenient. I'll shoot 35mm SLR or digital, but for that hair shirt experience I'll go to folders and TLRs...